35044-68-9

Usage

Uses

Used in Perfumery:
ALPHA-DAMASCONE is used as a fragrance ingredient in perfume compositions, particularly in rose perfumes, to impart a natural and complex fruity scent.
Used in Flavor Industry:
ALPHA-DAMASCONE is used as a flavoring agent in the flavor industry to add naturalness and body to various food products. It is found in a variety of foods, including bilberry, butter, milk, caviar, chicken fat, cooked beef and mutton, cured pork, pork and beef fat, roasted filberts and peanuts, pecans, potato chips, soybean, coriander leaf and seed, and kiwifruit.
Used in the Synthesis of Damascones:
ALPHA-DAMASCONE can be used as a starting material in the synthesis of other damascones, which are also used in perfumery and flavor industries. One synthetic route to the damascones starts with an appropriate cyclogeranic acid derivative, which is reacted with an allyl magnesium halide to give 2,6,6-trimethylcyclohexenyl diallyl carbinol. ALPHA-DAMASCONE, upon pyrolysis, yields the desired l-(2,6,6-trimethylcyclohexenyl)-3-buten-l-one, and damascone is obtained by rearrangement of the double bond in the side chain.

Preparation

Various methods: recently from ionone izoxazoles, also from 7,8-dehydro-β-ionole.

Upstream product

• 35124-05-1 2,6,6-Trimethyl-α-(1-propenyl)-1-cyclohexene-1-methanol 
• 23726-90-1 (Z)-2,6,6-Trimethyl-α-(1-propenyl)-1-cyclohexene-1-methanol 
• 39190-06-2 β-ionone isoxazole 
• 39900-12-4 1-(2,6,6-trimethyl-1-cyclohexenyl)-1,3-butanedione 
• 39900-16-8 2,6,6-trimethyl-1-[3-hydroxy-butan-1-oyl]-cyclohex-1-ene 
• 25915-53-1 2,6,6-trimethyl-3-cyclohexenyl methyl ketone 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 1197-92-8 1-(2,6,6-trimethyl-cyclohex-1-enyl)-ethanone 
• 75-07-0 acetaldehyde 
• 472-80-0 beta-Ionol 
• 79-77-6 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one 
• 124572-60-7 β-ionone epoxyhydrazone 
• 38448-31-6 β-ionone epoxide 

Downstream Products

• 23696-85-7 1-(2,6,6-trimethyl-1,3-cyclohexadiene-1-yl)-2-butene-1-one 

Relevant academic research and scientific papers

Synthesis process of beta-damascenone

The invention belongs to the technical field of chemical synthesis of perfume essences and in particular relates to a novel synthesis process for industrial production of beta-damascenone. The synthesis process comprises the following steps: by taking 1,3-pentadiene as a starting material, performing a Diels-Alder addition reaction on the 1,3-pentadiene with 4-methyl-3-pentene-2-one under catalysis of AlCl3 firstly so as to generate 1-(2,6,6,-trimethyl cyclohexyl-3-alkenyl)-butanone; under the catalysis of a solid super strong acid catalyst, performing olefin isomerization so as to obtain 1-(2,6,6,-trimethyl cyclohexyl-1-alkenyl)-butanone; and finally, performing a hydroxyaldehyde condensation reaction with acetaldehyde, so as to generate a target product, namely beta-damascenone. The synthesis process provided by the invention has the main advantages that the raw material cost is low, the energy consumption is low, a gas-phase reaction catalyzed by the solid super strong acid catalystis implemented in an olefin isomerization production process, the product purity is high, no reaction solvent is needed, a very small amount of wastewater or waste gas is generated, and in addition,the catalyst is good in reuse performance.

Preparation method of damascenone

The invention relates to the field of fine chemistry of perfume and discloses a preparation method of damascenone. The preparation method comprises following steps: step 1, beta-ionone oxime is takenas a raw material and dissolved in an organic alcohol solvent, then a metal halide solution and a catalytic amount of elemental halogen are added, the reaction solution is heated to a certain temperature, peroxide is dropwise added, a stirring reaction is performed after peroxide is dropwise added, and a beta-ionone oxime isoxazole derivative is obtained after the reaction; step 2, after the beta-ionone oxime isoxazole derivative is dissolved in the solvent, organic alcohol and a catalyst are added, stirred and dissolved, hydrogen is introduced by negative-pressure nitrogen displacement, the solution is heated to a certain temperature and subjected to a reaction, and damascenone is obtained after the reaction. Consumption of halogen with high pollution and high corrosivity is avoided in the synthetic route, an efficient organic metal complex is screened in the step 2 and serves as the catalyst, high-pressure hydrogen is utilized for reduction, so that consumption of metallic sodium isavoided, and safety of the synthetic route in the industrial production is improved.

1 - (2, 6, 6 - trimethyl - cyclohexenyl) - 2 - butene - 1 - ketone

The invention provides a 1-(2,6,6-trimethyl-cyclohexenyl)-2-buten-1-one preparation method, which comprises that 1-(2,6,6-trimethyl-3-cyclohexenyl)-1,3-butanedione is subjected to isomerization to obtained an isomerized product; and the isomerized product reacts to obtain 1-(2,6,6-trimethyl-cyclohexenyl)-2-buten-1-one, wherein the 1-(2,6,6-trimethyl-cyclohexenyl)-2-buten-1-one comprises 1-(2,6,6-trimethyl-cyclohex-1-enyl)-2-buten-1-one and 1-(2,6,6-trimethyl-cyclohex-2-enyl)-2-buten-1-one. According to the present invention, the 1-(2,6,6-trimethyl-3-cyclohexenyl)-1,3-butanedione is adopted as the raw material, such that the oxidation of the alcohol into the ketone is avoided compared with the prior art, and the environmental pollution is low; and the route is simple, and the scale production is easily achieved.

Industrial manufacturing method for damascenone

The invention provides an industrial manufacturing method for damascenone. The industrial manufacturing method for damascenone is characterized in that ionone serves as an initial raw material, and the target product damascenone is obtained after reducing, a rearrangement reaction, hydrolysis, oxidation and a hydrolysis reaction. The production process and the synthesis route are optimized; in the production process, there are fewer side reactions, aftertreatment is convenient, production conditions are mild, and the method is suitable for industrial production patterns.

A β- malaysian ketene method for the preparation of perfume

The invention discloses a preparation method of beta-damascenone spice. The preparation method comprises the following steps: (1) by taking beta-ionone as an initial raw material, carrying out a reaction with hydroxylamine hydrochloride in an alkaline environment to obtain beta-ionone oxime; (2) carrying out a reaction on beta-ionone oxime and halogens and metal salt thereof to obtain a beta-ionone oxime isoxazole derivative; (3) acting on the eta-ionone oxime isoxazole derivative and sodium to generate beta-dihydrodamascenone; and (4) carrying out an oxidizing halogenating reaction on beta-dihydrodamascenone and free radicals of halogens and carrying out an elimination reaction of removing halogen hydride under the alkaline environment to obtain the beta-damascenone. The preparation method disclosed by the invention is cheap and easily available in raw materials, simple to operate, mild in reaction condition, high in yield of reactions and low in cost, and the solvent used can be recycled, so that the preparation method is a method suitable for industrially producing beta-damascenone spice.

Precursors for fragrant ketones and fragrant aldehydes

The present invention refers to fragrance precursors of formula I for a fragrant ketone of formula II and one or more fragrant aldehydes or ketones of formula III and IV, These fragrance precursors are useful in perfumery, especially in the fine and functional perfumery.

Ketone precursors for organoleptic compounds

The invention discloses ketones of formula I: wherein, Y is an optionally substituted alkyl, cycloalkyl, or cycloalkylalkyl, wherein each alkyl group is straight or branched and each alkyl and cycloalkyl group is saturated or unsaturated; R1is hydrogen or a C1-6alkyl group that is substituted, saturated or unsaturated, straight or branched; A is a chromophoric substituted aromatic ring or ring system; n is an integer; and with the proviso that formula I is not 2-ethoxy-1-phenyl-ethanone. These compositions are useful for the delivery of organoleptic compounds, especially of flavors, fragrances, masking agents and antimicrobial compounds.

NEW DEVELOPMENTS OF THE WHARTON TRANSPOSITION

The synthetically useful Wharton transposition can be improved by using a more adequate procedure in the critical step of the intermediate α-epoxyhydrazone cleavage.Either for stable hydrazones or unstable ones, the yield of the transposed allylic alcohol is increased by treatment under anhydrous conditions with highly basic reagents (KDA in the former case, NEt3 in the latter).

OXIDATION OF ALCOHOLS BY ELECTROCHEMICALLY REGENERATED NICKEL OXIDE HYDROXIDE. SELECTIVE OXIDATION OF HYDROXYSTEROIDS

Primary alcohols, α,ω-diols and secondary alcohols are easily transformed into carboxylic acids, dicarboxylic acids or ketones, respectively, by heterogeneous oxidation with nickel oxide hydroxide electrochemically regenerated at a nickel hydroxyde electrode.The results are discussed in comparison to those of the nickel peroxide and chromic acid oxidation.The oxidation rate decreases with increasing steric hindrance of the alcohol, thus allowing the selective oxidation of the 3-position in hydroxysteroids.